Episode 44: When should you quit your day job?

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It’s THE question for every entrepreneur trying to turn their side business into their main livelihood – when should you quit your day job and pull the plug on a regular paycheck? The internet is full of encouragement to “take the leap,” but I don’t think that tells the whole story when it comes to such a difficult and complex decision. In today’s episode, two previous guests on the show talk about the struggles of quitting their day jobs and give some great advice for others considering it.


  • Why Alex did NOT take a big leap of faith… and what he did instead (3:30)
  • The importance of considering longevity in both business and life (5:05)
  • What to do if all your mental energy is spent on your day job (10:09)
  • How Kristi tried to quit three times before finally cutting ties – and what her first year of full self-employment was like (15:46)
  • Determining your level of risk tolerance (19:57)
  • What happens if everything goes wrong after you quit? (24:52)